Beckmann rearrangement products of methyl 3-oxo-tirucall-8, 24-dien-21-oate from Boswellia serrata gum and their anti-tumor activity |
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| Affiliation: | 1. Material Research Laboratory, Department of Chemistry, C.B. Khedgi’s Basaveshwar Science Raja Vijaysinh Commerce and Raja Jaysinh Arts College, Akkalkot, 413216, India;2. Thin Film Research Laboratory, Department of Chemistry, Institute of Science, Nagpur, 440001, India;3. Department of Chemistry, Doodhsakhar Mahavidyala Bidri, Kolhapur, 416208, India;1. Section of Electronic Physics and Systems, Department of Physics, National and Kapodistrian University of Athens, Athens, 15784, Greece;2. University of Novi Sad, Faculty of Technical Sciences, Department of Power, Electronics and Communications Engineering, Trg Dositeja Obradovica 6, 21000, Novi Sad, Serbia;3. University of Nis, Faculty of Electronic Engineering, Department for Telecommunications, A. Medvedeva 14, 18000, Nis, Serbia;4. Laboratory of Nonlinear Systems - Circuits & Complexity, Department of Physics, Aristotle University of Thessaloniki, GR-541 24, Thessaloniki, Greece;1. Research Center for Advanced Materials Science (RCAMS), King Khalid University, Abha, 61413, P.O. Box 9004, Saudi Arabia;2. The Smart Materials Research Institute, Southern Federal University, Sladkova 178/24, 344090, Rostov-on-Don, Russia;3. Department of Physics, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt;4. Physics Department, Faculty of Science, Zagazig University, 44519, Zagazig, Egypt;5. Nanoscience Laboratory for Environmental and Biomedical Applications (NLEBA), Semiconductor Lab., Physics Department, Faculty of Education, Ain Shams University, Cairo, Egypt;6. Advanced Functional Materials & Optoelectronic Laboratory (AFMOL), Department of Physics, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, Saudi Arabia;7. Department of Physics, Faculty of Science, Al-Azhar University, Assiut 71542, Egypt;1. Showa Pharmaceutical University, Machida, Tokyo 194-8543, Japan;2. Department of Pharmaceutical Science, Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama, Kanagawa 245-0066, Japan;1. Tissue Pathology and Diagnostic Oncology, Royal Prince Alfred Hospital, and NSW Health Pathology, Sydney, NSW, Australia;2. Melanoma Institute Australia, The University of Sydney, Sydney, NSW, Australia;3. Faculty of Medicine, University of New South Wales, Sydney, NSW, Australia;4. Department of Dermatology, University Hospital Zurich, Zurich, Switzerland;5. Faculty of Medicine and Health, The University of Sydney, Sydney, NSW, Australia;6. Department of Anatomical Pathology Department, Concord Repatriation General Hospital, and NSW Health Pathology, Sydney, NSW, Australia;7. Royal North Shore and Mater Hospitals, Sydney, NSW, Australia |
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| Abstract: | 3-Oxo-tirucall-8, 24-dien-3-one-21-oic acid is a minor natural product isolated from Boswellia serrata gum apart from β-boswellic acids. Since oxidation of 3-hydroxy group of β-boswellic acids leads to unstable beta-keto acids, Beckmann rearrangement could not be tried. Hence A-ring modified 3-oxo-tirucall-8, 24-dien-21 methyl esters (2–6) were synthesized for the first time via Beckmann rearrangement and evaluated for their anticancer potential against five human cancer cell lines (MCF-7, SW-982, HeLa, PC-3 and IMR-132) by MTT assay. While naturally occurring 3-oxo-tirucallic acid (1) and its methyl ester (2) exhibited nearly the same antiproliferative activity, A-ring modified molecules displayed improved anti-tumor activity with methyl A-homo-4-aza-3-oxo-tirucall-8, 24, dien-3-one-21-oate (4) exhibiting significant effect against prostate cancer cell lines. |
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| Keywords: | 3-Oxo-tirucallic acid Beckmann rearrangement Anti-tumor activity |
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